Effect of Bronsted acid co-catalyst in asymmetric conjugate addition of 3-aryloxindoles to maleimide under base-free phase-transfer conditions

被引：26

作者：

Shirakawa, Seiji

Makino, Hiroki

Yoshidome, Tomofumi

Maruoka, Keiji ^{[1
]}

机构：

[1] Kyoto Univ, Lab Synthet Organ Chem, Grad Sch Sci, Dept Chem,Sakyo Ku, Kyoto 6068502, Japan

来源：

TETRAHEDRON | 2014年 / 70卷 / 40期

关键词：

Phase-transfer catalysis; Organocatalysis; Asymmetric catalysis; Conjugate addition; Bronsted acid; ALKYL-ALPHA-AMINO; TRANSFER CATALYSTS; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; AMMONIUM-SALTS; ALDOL REACTION; SCHIFF-BASE; DESIGN; PERFORMANCE; OXINDOLES;

D O I：

10.1016/j.tet.2014.06.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly diastereo- and enantioselective conjugate addition of 3-aryloxindoles to maleimide was accomplished under base-free phase-transfer conditions. The effect of Bronsted acid co-catalyst was examined, and we found that the use of a phenol derivative as co-catalyst was effective for obtaining the target conjugate adduct in good yield with high stereoselectivity. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：7128 / 7132

页数：5

共 12 条

[1] Asymmetric phase-transfer reactions under base-free neutral conditions
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[2] Diastereo- and enantioselective conjugate addition of α-substituted nitroacetates to maleimides under base-free neutral phase-transfer conditions
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